How To Spend A Festive Three-Day Holiday Weekend in Sea Island

Most likely, you already know about Sea Island, the old-school resort where presidents and world leaders have vacationed for generations. I can’t imagine that many people visit the elegant and refined hideaway once. Rather, Sea Island inspires return visits, year after year, that become woven into a family’s lore and tradition.

Having visited Sea Island for both New Year’s and Mother’s Day, I feel compelled to make a declaration that, in addition to being an ideal family vacation destination, it’s the perfect escape for a three-day holiday weekend. Whether it’s Easter, Memorial Day, Father’s Day, Fourth of July, Thanksgiving, or Christmas, Sea Island knows how to set the scene for a celebratory weekend to remember. By simply being on property during a holiday weekend, guests know that Sea Island will execute every imaginable detail with precision and a bit of retro whimsy.

From Houston and Dallas, visitors can fly directly to either Jacksonville or Savannah and book the resort’s car service for the less-than-an-hour drive to the private island accessible only to Sea Island homeowners, members, and hotel guests. It’s a piece of cake. We’ve already given you the skinny on Sea Island’s history and layout, so let’s dive into why it’s worth returning to, year after year, for moments of celebration and relaxation.

Activities That Always Hit the Mark

Sea Island offers a robust selection of activities and excursions, from pickleball and paddleboarding to fishing and falconry. (ICYMI, there is perhaps no one who enjoys falconry, “the sport of kings,” more than me.) Though a City Mouse by birth, I certainly possess a few Country Mouse proclivities. When I planned my three-day holiday to Sea Island, I knew my itinerary needed to include a group lesson at their celebrated Shooting School. Before I try something new, I wonder whether I will be terrible or a savant; there is no in-between. (A few years ago, I asked my mother if she thought I might be a child prodigy when it came to some new hobby. Without missing a beat, she replied, “You’re 37.”)

All hat and no cattle, my friend Helen and I showed up to our lesson in cowboy boots, ready to roll. The Shooting School includes a five-stand sporting clay field, two skeet ranges, and a trap field. I assume our instructor, Jimmy, was an actual Child Prodigy. I cannot underscore how excellent a teacher he is; I think he could make anyone feel capable. In 90 minutes, Helen and I went from novices to smoking those clay pigeons. The Shooting School ended up being our favorite part of the trip, and you should absolutely schedule a session if it piques your curiosity at all.

Two non-negotiable, quintessentially Sea Island experiences? Bingo and the bagpiper!

Highland Park hive, rise up. You hear the word “bagpiper,” and you say “Hold my Sancerre!” Offered year-round on the terrace of The Lodge, diners and guests enjoy a traditional Scottish bagpiper sunset serenade that formally marks the end of each day at the Sea Island Golf Club. Perhaps the single most cherished Sea Island tradition, though, is B-I-N-G-O! For more than 50 years, guests have enjoyed rousing games of Bingo at The Cloister. Very little has changed during those five decades, which is what makes it feel special. That, and the fact that guests “dress for the occasion,” with men in jackets and collared shirts and the ladies in cocktail attire. It’s all very The Marvelous Mrs. Maisel in the best way possible. A can’t-miss favorite for all ages.

In addition to a family pool and bridge pool with a 20′ waterslide, Sea Island offers an adult-only pool. That is, of course, where you could find me. One common piece of travel advice I always offer — splurge and rent the private cabana! At the adult-only pool, our air-conditioned private cabana also included four poolside chaise lounges underneath umbrellas, ensuring optimal position in the sun or shade. Inside the cabana (which costs $900 to $1,200/day), there’s a TV, a stocked refrigerator of cold drinks, a colorful fruit platter, and a private bathroom with a shower. Worth every penny, especially if you plan to spend the whole day in the sun, including ordering a poolside lunch (the best).

Before my last visit, a well-traveled friend declared The Spa at Sea Island her favorite spa in the world. Challenge accepted! I can happily confirm that the Forbes Five-Star Spa lives up to the hype, starting with the magnificent relaxation garden in the atrium. In addition to a transcendent massage, I loved utilizing the amenities, which included a eucalyptus steam room, mineral soaking tubs, and vitamin C and aromatherapy-infused showers.

Dining That’s a Cut Above the Rest

After arriving at Sea Island, there is quite literally no reason to leave the property, especially because the dining options are so fabulous. In addition to the fanciest restaurant on the property, the Georgian Rooms (which is the perfect place for parents to sneak away on a date night!), allow me to highlight my personal favorites:

• Colt & Alison, located at The Lodge, functions as the resort’s classic steakhouse. It’s elegant and elevated, refined yet refreshed. “And for the lady, perhaps a filet mignon?” (What’s a girls’ weekend without a steak night?) To prime our palates, Helen and I started with the Onion Soup and Steakhouse Caesar Salad. To accompany our steaks, we… went a little ham on the side selections. Crispy Creamed Corn! Whipped Potatoes! Spinach with sunchoke butter and chips! After a day in the sun, we enjoyed getting dressed up for such a dignified dinner, which ended up being my favorite meal of the trip.
• Tavola, centrally located in The Cloister, bills itself as “rustic Italian cuisine with Southern charm,” and I think it delivers on that promise. Like so many things at Sea Island, the dishes — including crispy pizzas and generous bowls of pasta — are best served family style. We particularly loved the Tavola pizza, with béchamel, house-made sausage, rapini, and aged gouda.
• Don’t skip The Cloister’s beloved River Bar & Lounge for a casual meal and, most importantly, the Gold Brick Sundae, a tradition worth keeping! As an ice cream sundae enthusiast, I can’t imagine a trip to Sea Island without indulging in a Gold Brick Sundae (which is glorified Magic Shell… retro whimsy, remember?).

When I visited during Mother’s Day weekend, Sea Island hosted a marvelous Mother’s Day brunch that was beautifully decorated with fresh florals. Everyone dressed to the nines and enjoyed the live music as they visited the decadent food stations, which were manned by the chefs… and their moms! Très charmant!

The next time you’re wondering where to celebrate, consider the tradition and elegance of Sea Island. Your first visit won’t be your last.